Tetrahydrofuran → N-{4-[(3-Chloro-4-fluorophenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

HRID 612081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612081
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1.[CH2:23]1C[O:26][CH2:25][CH2:24]1.C(N(CC)CC)C.C(Cl)(=O)C=C>CN(C=O)C>[Cl:22][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:25](=[O:26])[CH:24]=[CH2:23])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][C:18]=1[F:21]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 110124336-Amino-4-[(3-chloro-4-fluorophenyl)amino]-3-quinolinecarbonitrile

Produkt 1

HCID 22466555N-{4-[(3-Chloro-4-fluorophenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolved 1.00 g (3.20 mmol) 6-amino-4-[(3-chloro-4-fluorophenyl)amino]-3-quinolinecarbonitrile in 2 ml hot DMF, added 12 ml THF and chilled to 0° C. under N2. Added 490 μl (3.52 mmol) triethyl amine and 295 μl (3.52 mmol) acryloyl chloride. Removed ice bath at 15 minutes, and at 1.5 hours stripped solvent. Slurried residue with a dilute sodium bicarbonate, collected solids, and washed with water. Recrystallized from ethyl acetate, giving 215 mg of yellow solid: mass spectrum (electrospray m/e): M+H=367.1, 369.1.

Aufarbeitung

  1. waitat 1.5 hours stripped
  2. customSlurried residue with a dilute sodium bicarbonate, collected solids
  3. washwashed with water
  4. customRecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1c9af908d403450c889c86f6c03d8c26
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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